Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship

Credit: Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock

Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship

Jon Cryer and Charlie Sheen were costars on Two and a Half Men for eight seasons until Sheen was fired from the hit sitcom in 2011. “In the early years, the life with Charlie Sheen was great,” Cryer told Entertainment Tonight in June 2022. Production for Two and a Half Men was halted twice, first in 2010 and then again in 2011, while the star attended rehab. Less than a week before Sheen was slated to return to the sitcom after his 2011 stint in rehab, he called into the Alex Jones radio show to rant about Lorre, calling him a “charlatan” and a “clown.” The Platoon actor also mocked Alcoholics Anonymous, calling it “a bootleg cult” with “a 5 percent success rate.” The following month, Sheen was fired from his top-rated series. Scroll through for a timeline of Cryer and Sheen’s ups and downs:

Credit: Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock

Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship

Jon Cryer and Charlie Sheen were costars on Two and a Half Men for eight seasons until Sheen was fired from the hit sitcom in 2011. “In the early years, the life with Charlie Sheen was great,” Cryer told Entertainment Tonight in June 2022. Production for Two and a Half Men was halted twice, first in 2010 and then again in 2011, while the star attended rehab. Less than a week before Sheen was slated to return to the sitcom after his 2011 stint in rehab, he called into the Alex Jones radio show to rant about Lorre, calling him a “charlatan” and a “clown.” The Platoon actor also mocked Alcoholics Anonymous, calling it “a bootleg cult” with “a 5 percent success rate.” The following month, Sheen was fired from his top-rated series. Scroll through for a timeline of Cryer and Sheen’s ups and downs:

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Things Started Out 'So Smoothly'

Two and a Half Men premiered on CBS in September 2003. “For those first couple of years, it was, you know, an incredible joy,” Cryer told Entertainment Tonight in 2022. “[Sheen] had been sober for two years when we started the show, and it was really important to him to keep sober. And for those first few years, the show was also going so smoothly.”

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Cryer Noticed There Was 'Trouble Brewing'

Cryer has said that he started to notice a change in Sheen after his 2006 divorce. “He was still lovely to work with, he still showed up on time and knew his lines and was doing the job. But you could tell that there was some trouble brewing,” he told ET in 2022.

He continued, "He started to have issues with the writing and sometimes issues with the writing that I didn't understand. I would say, 'This is the kind of joke you had no problem with a year and a half ago, and suddenly now it's an issue?' So, you know, it was very subtle. It took a while before it started really going off the rails."

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Sheen Slammed Lorre on the Radio

In February 2011, Sheen called the creator of Two and a Half Men a “charlatan” and a “clown” during a live Alex Jones radio show.

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Sheen Was Fired From 'Two and a Half Men'

The Arrival actor was fired from his CBS sitcom in March 2011. Ashton Kutcher was hired to join the cast the following season to fill the void.

“I think, actually, when Charlie was let go from the show, the first thought amongst most of us was, 'OK, we're done. This has been a great thing, but we're done at this point,’” Cryer told ET in 2022.

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'Two and a Half Men' Ended in 2015

After 12 seasons, eight of which Sheen appeared in, Two and a Half Men came to an end in February 2015.

In the series finale, Sheen’s character, played by a body double whose face is never shown, returns to his former home only to be crushed by a falling piano.

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Sheen Reflected On the Events That Led to His Firing

In February 2021, the Golden Globe winner reflected on the behavior that led to his firing from Two and a Half Men.

“I think it was drugs or the residual effects of drugs … and it was also an ocean of stress and a volcano of disdain. It was all self-generated, you know,” he told Yahoo! Entertainment.

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Cryer Joked About a Reunion With Sheen

Although Sheen called his former costar a “traitor” and a “troll” after he was fired from their CBS series, Cryer doesn’t have any hard feelings.

In June 2022, the Arrow alum tweeted, “Just Saw Top Gun: Maverick. Think it’s time to reunite with Sheen for Hot Shots: Part Tres.”

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Not Ruling Out a Reboot

“I’m not going to rule anything out,” Cryer said of a Two and a Half Men reboot with Sheen during a December 2023 interview with Entertainment Tonight. "I have not spoken to Charlie. I don't know that he knows my number anymore. But anything could happen."

The actor also reacted to Lorre and Sheen ending their feud.

“I’m really glad they made up,” Cryer told the outlet. “I can only [speak] for Chuck, clearly. He has the enormous relief of somebody who's been able to rekindle a friendship that was really meaningful to him."

Sheen appeared as a version of himself in Lorre’s Max series Bookie, which premiered in November 2023. Ahead of the show’s premiere, Lorre told Variety that his first conversation with Sheen about the project was “healing” for him.

“Almost as soon as we started talking, I remembered, we were friends once,” he said. “And that friendship just suddenly seemed to be there again. I don’t want to be too mawkish about it, but it was healing. And he was also totally game to make fun of himself.”

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Speaking Out

Cryer reflected on his time working with Sheen in his September 2025 Netflix doc. "He's in the midst of falling apart in every way I can imagine and he's renegotiating his contract for another year of a show I am supposed to be on too. Apparently they had pre-sold a couple of extra seasons of the show. It was worth their while to spend this astonishing amount of money on Charlie," Cryer recalled. "[Charlie's] negotiations went off the charts because his life was falling apart. Me, whose life was pretty good at that time, I got a third of that."

After hearing what Cryer had to say in his doc, Sheen praised his “really insightful” and “compassionate” words. 

“It was really cool to hear from his perspective. He was in the line of fire with all that stupid s*** going on, and it was affecting him and his family and his career and all that. I can’t debate anything that he said," Sheen told People. “He nailed that, and I’m so glad he opened that door, because it gave me a chance to really start thinking about that. He said, ‘He’s a guy that doesn’t believe he deserves the things he has, or that it was he earned,’ and I was like, ‘Whoa.'”

Sheen acknowledged that Cryer made some important points. 

“Suddenly, I felt like I was on a couch in Jon’s therapy office, and he was dead on. That’s something that I’ve felt my whole life, because I had no formal training. I had no formal education, I didn’t even finish high school," he explained. "And suddenly I’m working and traveling, I’m a star and all this stuff. It just happened. There was no plan. And there was always the voice of doubt there, telling me it’s only a matter of time before this all goes away, so to enjoy this as heartily as you can."

Sheen also revealed he didn't personally ask Cryer to participate because he didn't have his number.